Preparation of novel reagents 4-alkoxytrityl chlorides and their reaction with methyl Α-d-glucoside

Abstract

A series of novel 4-O-alkoxytrityl chlorides (1) with different chain lengths was synthesized as a novel reagent for obtaining 6-O-alkylated cellulose with high regioselectivity via trityl groups in one reaction step without the use of any protective groups. These chlorides were reacted with methyl Α-d-glucoside, which was used as a model compound, to examine the reactivities toward the primary hydroxyl groups of cellulose to afford a series of 6-O-alkylated methyl Α-d-glucosides in high yields. The product compounds were found to have interesting solubilities and thermal properties. Thus, newly prepared trityl chloride derivatives were found to be useful regioselective derivatization reagents on the primary hydroxyl group in carbohydrates, especially in cellulose.